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I'henylhydra/ones <".re not formed, .as phcnylfiydrazine acts as a
reducing ;igent and produces quinol.^

The constitution of quinhydrohe. tfep intermediate
formed by the reduction of quinoneS,^ <&\da&jq<ft», oT""
represented by the formula,                     ^^^^IJ. ~ ^.«*•-••••


" 4\ nc\Jui

For the formation of dimcthylquinone, sec p. 251.

Pkl<: PA RATION    86.

Benzyl Chloride.--The action of chlorine on boiling
toluene is quite distinct from the action which occurs in the
rold or in presence of a u halogen carrier " (see pp. 252, 271).
In the present instance substitution takes place in the side-
chaiu. It is a curious fact, however, that: clllorinc produced by
elect rolysis \\\ presence of boiling toluene mainly enters the

P.y prolonged action all three hydrogen atoms of the side-chain
may be replaced, and the following compounds obtained: —
Ct.lI,(ClU;i     Ben/yl Chloride.
(',';! r,CI ICK,    iJciixal Chloride.
C,jII..(CCl.,       ncny.otridiloride.

Hydrocarbons containing the halogen in the side-chain may
be L'.cncrany, though not. invariably distinguished, by their
irritating action on the eyes and mucous membrane of the nose,
from those in which the halogen is present in the nucleus.
Moreover, the halogen in the side-chain is much more readily
substituted or removed than when it occurs in the nucleus. In
this respect the above compounds resemble the members of the
aliphatic series (alkyl and alkylene halides). Benzyl chloride is
decomposed by water, ammonia, and potassium cyanide, forming
ben/yl alcohol, ben/yl cyanide, and benzylamine.

c,;ii,ciu:i ! ju) - (Viir,cii,OTi -i- nci
c(iH,cn,ci i KCN .- (;,,nBciiaCN + KCL

Jlcn/yl cyatiidf,

(VJI^'H-/1!  I  2NII:,.....C.-HnCH.jN'IIo •)  NH4C1.